4-(Cyclohexylamino)-1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidine-4-carbonitrile | 1026321-49-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-(Cyclohexylamino)-1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidine-4-carbonitrile
• CAS: 1026321-49-2
• 化学式: C₂₄H₃₄FN₃O₂
• 分子量: 415.551
• InChiKey: SCSFKRQPFGSBII-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(Cyclohexylamino)-1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidine-4-carbonitrile 在 硫酸 作用下， 生成 4-Cyclohexylamino-1-[4-(4-fluoro-phenyl)-4-oxo-butyl]-piperidine-4-carboxylic acid amide
  参考文献：
  名称：

  Spiperone:  Influence of Spiro Ring Substituents on 5-HT_2A Serotonin Receptor Binding

  摘要：

  Spiperone (1) is a widely used pharmacological tool that acts as a potent dopamine D-2, serotonin 5-HT1A, and serotonin 5-HT2A antagonist. Although spiperone also binds at 5-HT2C receptors, it is one of the very few agents that display some (ca. 1000-fold) binding selectivity for 5-HT2A versus 5-HT2C receptors and, hence, might serve as a useful template for the development of novel 5-HT2A antagonists if the impact of its various substituent groups on binding was known. In the present investigation we focused on the 1,3,8-triazaspiro[4.5]decanone portion of spiperone and found that replacement of the N-1-phenyl group with a methyl group only slightly decreased affinity for cloned rat 5-HT2A receptors. However, N-1-methyl derivatives displayed significantly reduced affinity for 5-HT1A, 5-HT2C, and dopamine D-2 receptors. Several representative examples were shown to behave as 5-HT2 antagonists. As such, N-1-alkyl analogues of spiperone may afford entry into a novel series of 5-HT2A-selective antagonists.

  DOI：

  10.1021/jm980452a
• 作为产物：
  描述：

  2-(3-氯丙基)-2-(4-氟苯基)-1,3-二氧戊烷 在 sodium carbonate 、 氯化铵 、 sodium iodide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 84.0h， 生成 4-(Cyclohexylamino)-1-[3-[2-(4-fluorophenyl)-1,3-dioxolan-2-yl]propyl]piperidine-4-carbonitrile
  参考文献：
  名称：

  Spiperone:  Influence of Spiro Ring Substituents on 5-HT_2A Serotonin Receptor Binding

  摘要：

  Spiperone (1) is a widely used pharmacological tool that acts as a potent dopamine D-2, serotonin 5-HT1A, and serotonin 5-HT2A antagonist. Although spiperone also binds at 5-HT2C receptors, it is one of the very few agents that display some (ca. 1000-fold) binding selectivity for 5-HT2A versus 5-HT2C receptors and, hence, might serve as a useful template for the development of novel 5-HT2A antagonists if the impact of its various substituent groups on binding was known. In the present investigation we focused on the 1,3,8-triazaspiro[4.5]decanone portion of spiperone and found that replacement of the N-1-phenyl group with a methyl group only slightly decreased affinity for cloned rat 5-HT2A receptors. However, N-1-methyl derivatives displayed significantly reduced affinity for 5-HT1A, 5-HT2C, and dopamine D-2 receptors. Several representative examples were shown to behave as 5-HT2 antagonists. As such, N-1-alkyl analogues of spiperone may afford entry into a novel series of 5-HT2A-selective antagonists.

  DOI：

  10.1021/jm980452a